AU2006347616A1 - Molecules with complexing groups for aqueous nanoparticle dispersions and uses thereof - Google Patents
Molecules with complexing groups for aqueous nanoparticle dispersions and uses thereof Download PDFInfo
- Publication number
- AU2006347616A1 AU2006347616A1 AU2006347616A AU2006347616A AU2006347616A1 AU 2006347616 A1 AU2006347616 A1 AU 2006347616A1 AU 2006347616 A AU2006347616 A AU 2006347616A AU 2006347616 A AU2006347616 A AU 2006347616A AU 2006347616 A1 AU2006347616 A1 AU 2006347616A1
- Authority
- AU
- Australia
- Prior art keywords
- particles
- composition
- dispersion
- group
- dispersant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000006185 dispersion Substances 0.000 title claims description 99
- 239000002105 nanoparticle Substances 0.000 title claims description 29
- 230000000536 complexating effect Effects 0.000 title description 2
- 239000002245 particle Substances 0.000 claims description 133
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 86
- 239000000203 mixture Substances 0.000 claims description 73
- 239000002270 dispersing agent Substances 0.000 claims description 49
- 239000007788 liquid Substances 0.000 claims description 44
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 37
- 229910044991 metal oxide Inorganic materials 0.000 claims description 34
- 150000004706 metal oxides Chemical class 0.000 claims description 34
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 18
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 14
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 13
- -1 amine compound Chemical class 0.000 claims description 13
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 10
- 229920000570 polyether Polymers 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 9
- 235000011187 glycerol Nutrition 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 150000003460 sulfonic acids Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 claims description 6
- 239000011787 zinc oxide Substances 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- 239000011976 maleic acid Substances 0.000 claims description 5
- JFXDYPLHFRYDJD-UHFFFAOYSA-M sodium;6,7-dihydroxynaphthalene-2-sulfonate Chemical compound [Na+].C1=C(S([O-])(=O)=O)C=C2C=C(O)C(O)=CC2=C1 JFXDYPLHFRYDJD-UHFFFAOYSA-M 0.000 claims description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 4
- 239000004642 Polyimide Substances 0.000 claims description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 239000002082 metal nanoparticle Substances 0.000 claims description 4
- 239000002923 metal particle Substances 0.000 claims description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920001721 polyimide Polymers 0.000 claims description 4
- 229920005591 polysilicon Polymers 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 claims description 4
- BWAUQTFFVCLSOS-UHFFFAOYSA-N sodiosodium hydrate Chemical compound O.[Na].[Na] BWAUQTFFVCLSOS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000004908 Emulsion polymer Substances 0.000 claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 claims description 3
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 claims description 3
- 239000000084 colloidal system Substances 0.000 claims description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229920001909 styrene-acrylic polymer Polymers 0.000 claims description 3
- 239000002344 surface layer Substances 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 230000006641 stabilisation Effects 0.000 claims description 2
- 238000011105 stabilization Methods 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- JYMITAMFTJDTAE-UHFFFAOYSA-N aluminum zinc oxygen(2-) Chemical compound [O-2].[Al+3].[Zn+2] JYMITAMFTJDTAE-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- ISWQCIVKKSOKNN-UHFFFAOYSA-L Tiron Chemical compound [Na+].[Na+].OC1=CC(S([O-])(=O)=O)=CC(S([O-])(=O)=O)=C1O ISWQCIVKKSOKNN-UHFFFAOYSA-L 0.000 description 32
- 239000012530 fluid Substances 0.000 description 29
- 239000007787 solid Substances 0.000 description 16
- 238000000576 coating method Methods 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 11
- 239000000976 ink Substances 0.000 description 10
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 8
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 7
- 230000001070 adhesive effect Effects 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- 125000000129 anionic group Chemical group 0.000 description 6
- 239000011859 microparticle Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000000527 sonication Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000002525 ultrasonication Methods 0.000 description 2
- XSXWOBXNYNULJG-UHFFFAOYSA-N 2-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC=C1O XSXWOBXNYNULJG-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- SZBYVOSSTHEBFR-UHFFFAOYSA-N 2-(2-methyloctan-2-yl)phenol Chemical compound CCCCCCC(C)(C)C1=CC=CC=C1O SZBYVOSSTHEBFR-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- VWXVJYKCCPSYRD-UHFFFAOYSA-N 4,6-dihydroxybenzene-1,3-disulfonic acid Chemical compound OC1=CC(O)=C(S(O)(=O)=O)C=C1S(O)(=O)=O VWXVJYKCCPSYRD-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- 101100361281 Caenorhabditis elegans rpm-1 gene Proteins 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229910003202 NH4 Inorganic materials 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006127 SO3X Inorganic materials 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000013590 bulk material Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 229960000878 docusate sodium Drugs 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- HGVHMIAKUYLQLL-UHFFFAOYSA-N ethene;propane-1,2,3-triol Chemical compound C=C.OCC(O)CO HGVHMIAKUYLQLL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000000696 magnetic material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011858 nanopowder Substances 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000006120 scratch resistant coating Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000012904 visual particle Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/0004—Preparation of sols
- B01J13/0043—Preparation of sols containing elemental metal
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/0004—Preparation of sols
- B01J13/0047—Preparation of sols containing a metal oxide
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/12—Sulfonates of aromatic or alkylated aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Colloid Chemistry (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
Description
WO 2007/082155 PCT/US2006/060151 TITLE OF THE INVENTION: MOLECULES WITH COMPLEXING GROUPS FOR AQUEOUS NANOPARTICLE DISPERSIONS AND USES THEREOF This Application claims the benefit of Provisional Application No. 60/730,735, filed on October 27, 2005 and Provisional Application No. 60/797,251, filed on May 02, 2006. The disclosure of these Provisional Applications is hereby incorporated by reference. CROSS-REFERENCE TO RELATED APPLICATIONS [0001] The subject matter herein is related to U.S. Patent Application No. 11/524,471, filed on September 21, 2006 and entitled "Use Of 2,3-Dihydroxynapthalene-6-Sulfonic Acid Salt As A Dispersant"; the disclosure of which is hereby incorporated by reference. 5 BACKGROUND OF THE INVENTION [0002] The invention relates to dispersions. In particular, the invention relates to stable dispersions of nanoparticles and microparticles in liquids and to methods for their preparation. [0003] Nanoparticles of Group IlIlA metal oxides, specifically, those of aluminum and 10 indium have important commercial applications. Nano alumina is of interest for scratch resistant coatings and heat transfer fluids. Additionally, aluminum metal nanoparticles that have been passivated with a thin layer of aluminum oxide are of use in the development of energetic materials. Indium tin oxide (ITO) nanoparticles have applications in clear conductive coatings, in heat management layers, and in static 15 charge dissipation. Zinc oxide and titanium oxide nanoparticles have applications in UV blocking sunscreens, coatings and textiles. Other applications of metal oxide nanoparticles and/or nanoparticles that have a metal oxide surface include magnetic materials, heterogeneous catalysts, toner compositions, and ceramics. [0004] In order to supply nanoparticles and/or microparticles as easy to use dispersion 20 master batches or in fully formulated compositions, the particles must be dispersed in various liquids and polymeric matrices. The quality of the dispersion must support its intended use. For example, the presence of color and opacity or haze are is -1 - WO 2007/082155 PCT/US2006/060151 unacceptable in many applications, including inks and coatings. In addition, the dispersion is preferably stable so it does not have to be prepared immediately before use, but can be stored after preparation. [0005] Currently, many nanoparticle dispersions are prepared by functionalizing the 5 surface of the particles with materials such as silanes. This approach uses expensive silanes and requires additional processing steps. Alternatively, ionic dispersants that rely upon electrostatic attraction for anchoring to the particle surface are used. Below the isoelectric point, where the nanoparticle is inherently cationic, an anionic dispersant is required to achieve surface anchorage. Above the isoelectric point, where the particle 10 is inherently anionic, a cationic dispersant is required. Consequently, the resulting dispersion can not tolerate a wide pH range. In addition, many materials used in coatings, inks, are anionic and not compatible with cationic materials. Thus, a need exists for stable dispersions of nanoparticles and/or microparticles particles of metal oxides and/or particles that have an metal oxide surface that do not have these 15 problems, and to methods for preparing these dispersions. BRIEF SUMMARY OF THE INVENTION [0006] The instant invention solves problems associated with conventional practices by providing a composition comprising a dispersion of particles in at least one liquid (e.g., at 20 least one polar liquid). [0007] In one aspect, the composition comprises: a) about 0.1 wt% to about 25 wt%, based on the total weight of the dispersion, of at least one dispersant comprising the formula: SO 3 Na OH HO
SO
3 Na 25 NaO 3 S OH HO b) about 1 wt% to about 90 wt%, based on the total weight of the dispersion, of particles comprising at least one member selected from the group -2- WO 2007/082155 PCT/US2006/060151 consisting of metal oxide particles, particles having a metal oxide surface, and mixtures thereof, in which the particles have a particle size of about 1 nm to about 2000 nm; and c) about 10 wt% to about 90 wt%, based on the total weight of the 5 dispersion, comprising at least one member selected from the group consisting of water, ethylene glycol, propylene glycol, glycerin, glycol mono-ethers of the formula R"OCH 2
CH
2 OH, in which R" is an alkyl group of one to four carbon atoms, and mixtures thereof. 10 [0008] In another aspect of the invention, the composition comprises: a) about 10 wt.% to about 90wt.% water, b) about 0.1 wt% to about 25 wt%, based on the total weight of the dispersion, of at least one dispersant selected from the group consisting of ortho dihydroxyaromatic sulfonic acid salts (e.g., having the previously identified 15 formula), and optionally at least one of the following: polyoxyethylenated long cain amines, polyoxyethylenated alkyphenols, polyoxyethylenated alcohols, polyoxyethylenated carboxylic acids, polyoxyethylenated sorbitol esters, polyoxyethylenated alkanolamides, long-chain carboxylic acid esters, poly(ethylene oxide-co-propylene oxide) and sulfonated, sulfated, phosphated or 20 phosphonated derivatives of the above; the class of materials known as polymeric dispersing agents which comprise certain polyacrylates, polyesters, polyamides, maleic acid/vinyl polyether copolymer, styrene-maleic acid copolymers, polyurethanes, polyimides, polyethers, polysilicones, as well as amine, alcohol, acid, ester and other functionalized derivatives of the previous list 25 and copolymers of the same, among others, c) about 1 wt% to about 90 wt%, based on the total weight of the dispersion, of particles comprising at least one member selected from the group consisting of metal oxide particles, particles having a metal oxide surface, and mixtures thereof, in which the particles have a particle size of about 1 nm to about 30 2000 nm; d) optionally about 10 wt% to about 90 wt%, based on the total weight of the dispersion, comprising at least one member selected from the group consisting of water, ethylene glycol, propylene glycol, glycerin, glycol mono -3- WO 2007/082155 PCT/US2006/060151 ethers of the formula R"OCH 2
CH
2 OH, in which R" is an alkyl group of one to four carbon atoms, and mixtures thereof, e) optionally about 1 wt% to about 99 wt%, based upon the total weight of the dispersion, comprising at least one member selected from the group 5 consisting of water-borne polymers such as emulsion polymers, aqueous polymer dispersions, aqueous polymer colloids, and aqueous polymer solutions. These water-borne polymers may comprise at least one of urethane, acrylic, styrene acrylic, siloxane, vinyl acetate, vinyl chloride and among other polymers; and; f) optionally all or part of the metal oxide nanoparticles can be replaced 10 with about 10 wt% to about 90 wt%, based on the total weight of the dispersion, comprising at least one member selected from the group of metal nanoparticles. [0009] In a further aspect of the invention, the dispersing agent comprises a compound having the formula: 15 S0 3 X R1 R2 R1 OH HO SO3X RO HO R5 NaO3S OH R3 R4 R2 wherein R1 -R4 comprise H and/or alkyl, and X comprises at least one member selected from the group consting of Na, K, Li, NH4, R1 NH2, R2NH, and R3N 20 [0010] These compositions find utility as binders, coatings, inks, and surface treatments in the textile, coatings, graphic arts, and personal care industries. [0011] In one aspect, the particles are nanoparticles, having an average diameter of about 1 nm to about 100 nm. In another aspect, the invention comprises a method for 25 preparing the dispersion by dispersing the particles in a liquid medium comprising at least one dispersant. -4- WO 2007/082155 PCT/US2006/060151 DETAILED DESCRIPTION OF THE INVENTION [0012] Unless the context indicates otherwise, in the specification and claims, the terms particles, metal oxide particles, particles having a metal oxide surface, dispersant, liquid, cation, and similar terms also include mixtures of such materials. Unless 5 otherwise specified, all percentages are percentages by weight and all temperatures are in degrees Centigrade (degrees Celsius). [0013] In one aspect the invention comprises a dispersion of particles having a particle size of about 1 nm to about 2000 nm in liquid. The particles comprise at least one member selected from the group consisting of metal oxide particles, particles having a 10 metal oxide surface, and mixtures thereof. The dispersion comprises the dispersant, the particles, and at least one liquid. [0014] In one aspect of the invention, the dispersant comprises at least one orthodihydroxyaromatic sulfonic acid salt such as disodium salt monohydrate of 4-5 dihydroxy-1,3 benzenedisulfonic acid typically having the following formula:
SO
3 Na OH 15 NaO 3 S OH or sodium 2,3-dihydroxy-6-naphthalene sulfonate typically having the following formula: HO SO 3 Na HO 20 [0015] Disodium salt monohydrate of 4-5-dihydroxy-1,3 benzenedisulfonic acid is commercially available from Merck AG under the trade name "Tiron". Sodium 2,3 dihydroxy-6-naphthalene sulfonate is available as a dye precursor sold under the name dihydroxy R salt Nantog Baisheng Chemicals Co. By using an effective amount of the inventive dispersant, a composition can be obtained having a viscosity of less than about 25 2000 centipoises (e.g., less than about 1000 centipoises). -5- WO 2007/082155 PCT/US2006/060151 [0016] In another aspect of the invention, the composition comprises: a) about 10 wt.% to about 90wt.% water, b) about 0.1 wt% to about 25 wt%, based on the total weight of the dispersion, of at least one dispersant selected from the group consisting of 5 orthodihydroxyaromatic sulfonic acid salts (e.g., having the previously identified formula), and optionally at least one of the following: polyoxyethylenated long cain amines, polyoxyethylenated alkyphenols, polyoxyethylenated alcohols, polyoxyethylenated carboxylic acids, polyoxyethylenated sorbitol esters, polyoxyethylenated alkanolamides, long-chain carboxylic acid esters, 10 poly(ethylene oxide-co-propylene oxide), and sulfonated, sulfated, phosphated or phosphonated derivatives of the above; the class of materials known as polymeric dispersing agents which comprise certain polyacrylates, polyesters, polyamides, maleic acid/vinyl polyether copolymer, styrene-maleic acid copolymers, polyurethanes, polyimides, polyethers, polysilicones, as well as 15 amine, alcohol, acid, ester and other functionalized derivatives of the previous list and copolymers of the same, among others, c) about 1 wt% to about 90 wt%, based on the total weight of the dispersion, of particles comprising at least one member selected from the group consisting of metal oxide particles, particles having a metal oxide surface, and 20 mixtures thereof, in which the particles have a particle size of about 1 nm to about 2000 nm; d) optionally about 10 wt% to about 90 wt%, based on the total weight of the dispersion, comprising at least one member selected from the group consisting of water, ethylene glycol, propylene glycol, glycerin, glycol mono 25 ethers of the formula R"OCH 2
CH
2 OH, in which R" is an alkyl group of one to four carbon atoms, and mixtures thereof, e) optionally about 1 wt% to about 99 wt%, based upon the total weight of the dispersion, comprising at least one member selected from the group consisting of water-borne polymers such as emulsion polymers, aqueous polymer 30 dispersions, aqueous polymer colloids, and aqueous polymer solutions. These water-borne polymers may comprise at least one of urethane, acrylic, styrene acrylic, siloxane, vinyl acetate, vinyl chloride and among other polymers; and; -6- WO 2007/082155 PCT/US2006/060151 f) optionally all or part of the metal oxide nanoparticles can be replaced with about 10 wt% to about 90 wt%, based on the total weight of the dispersion, comprising at least one member selected from the group of metal nanoparticles. 5 [0017] In a further aspect of the invention, the dispersant comprises a medium comprising water, one dispersant selected from the group consisting of orthodihydroxyaromatic sulfonic acid salts (e.g., having the previously identified formula), and optionally at least one of the group consisting of polyoxyethylenated long-cain amines, polyoxyethylenated alkyphenols, polyoxyethylenated alcohols, 10 polyoxyethylenated carboxylic acids, polyoxyethylenated sorbitol esters, polyoxyethylenated alkanolamides, long-chain carboxylic acid esters, poly(ethylene oxide-co-propylene oxide), and sulfonated, sulfated, phosphated or phosphonated derivatives of the above; polymeric dispersing agents which comprise at least one member from the group of polyacrylates, polyesters, polyamides, maleic acid/vinyl 15 polyether copolymer, styrene-maleic acid copolymers, polyurethanes, polyimides, polyethers, polysilicones, as well as amine, alcohol, acid, ester and other functionalized derivatives of the previous list and copolymers of the same, among others. [0018] In another aspect, at least one the inventive dispersion can further comprise at least one latex compound such as latexes derived from the following monomers used 20 either alone or in combination: acrylate esters, acrylic acid, methacrylate esters, methacrylic acid, acrylonitrile, ethylene, styrene, butadiene, vinyl chloride, vinyl acetate. For example, the inventive composition can comprise nanoparticles, at least one orthodihydroxyaromatic sulfonic acid salt, at least one latex and at least one non-ionic copolymer with carboxy anchor groups, pH = 7 (e.g., Disperbyk-1 90). 25 [0019] Desirable results have been obtained by using a dispersant comprising a medium comprising water, an orthodihydroxyaromatic sulfonic acid salt, and at least one of the foregoing optional components. By using an effective amount of such dispersant(s) a composition can produced having electrostatic and steric stabilization. [0020] The dispersion comprises microparticles and/or nanoparticles. Nanoparticles 30 generally refers to particles that have an average diameter of about 100 nm or less, typically between about 100 nm and about 1 nm. Nanoparticles have an intermediate size between individual atoms and macroscopic bulk solids. Because of their relatively small size, the physical and chemical properties of nanoparticles, especially those of -7- WO 2007/082155 PCT/US2006/060151 nanoparticles smaller than about 50 nm, may differ measurably from those of the bulk material. Microparticles are larger than nanoparticles. They have an average diameter of about 100 nm (0.1 micron) to about 100 microns. The dispersion typically comprises particles that have an average diameter of about 2000 nm or less, typically an average 5 diameter of about 1 nm to about 2000 nm. Typically greater than about 50% of the particles are less than 100nm and normally greater than about 90% of the particles are less than 100nm (e.g., 95% of the particles are less than 100nm). [0021] Particle size refers to the size of the particles determined by the BET (Brunauer, Emmet, Teller) method. This method, which involves adsorbing a monolayer of liquid 10 nitrogen onto the surface of a mass of particles, then measuring the amount of nitrogen released when that monolayer is vaporized, is well known to those skilled in the art. The particle size measured for the particles in the dispersion, which is measured by other methods, may be larger than the particle size determined by the BET method because of aggregation of the primary nanoparticles into aggregates. As discussed below, the 15 particle size measured for the particles in the dispersion is a measure of the ability of the dispersing agent to produce a dispersion. [0022] The particles comprise at least one member selected from the group consisting of metal oxide particles, particles having a metal oxide surface, and mixtures thereof. Although the metal oxide particles may be particles of any metal oxide that forms the 20 dispersion, typical metal oxides comprise at least one member selected from the group consisting of alumina (A1 2 0 3 ), indium tin oxide (a mixture comprising In 2 0 3 and SnO 2 ), zirconia (ZrO 2 ), titania (TiO 2 ), iron oxide (Fe 2 0 3 ), ceria (CeO 2 ), zinc oxide (ZnO), and mixtures thereof. More typically, the metal oxide comprises alumina or indium tin oxide. The metal oxide particles may be doped with other materials. Typical particles having a 25 metal oxide surface include aluminum metal particles with a surface layer of aluminum oxide. [0023] The liquid may be any liquid (e.g., a polar liquid) in which the dispersion may be formed. Typical liquids comprise at least one member selected from the group consisting of water, ethylene glycol, glycerin, propylene glycol, ethylene glycol mono 30 ethers, and mixtures thereof. Typical ethylene glycol mono-ethers are compounds of the structure R"OCH 2
CH
2 OH, in which R" comprises an alkyl group of one to four carbon atoms, such as methyl, ethyl, n-propyl, or n-butyl. Common ethylene glycol mono-ethers include 2-methoxyethanol (methyl CELLOSOLVE@) and 2-butoxyethanol (butyl -8- WO 2007/082155 PCT/US2006/060151 CELLOSOLVE@). In some cases, the composition is substantially free of water or the composition is prepared (e.g., as a "master batch"), and then added to water. By substantially free of water it is meant the composition contains less than about 1 wt.% water. 5 [0024] Typically, the dispersion comprises about 0.1 wt% to about 25 wt% of the dispersant, about 1 wt% to about 90 wt% of the particles, and about 10 wt% to about 90 wt% of the liquid, based on the total weight of the dispersion. More typically the dispersion comprises about 0.1 wt% to about 10 wt% of the dispersant, about 5 wt% to about 80 wt% of the particles, and about 5 wt% to about 80 wt% of the liquid, based on 10 the total weight of the dispersion. Most typically the dispersion comprises about 0.1 wt% to about 5 wt% of the dispersant, about 10 wt% to about 70 wt% of the particles, and about 25 wt% to about 75 wt% of the liquid, based on the total weight of the dispersion. Typically, the dispersant, the particles, and the liquid together make up at least about 95 wt%, more typically at least about 98 wt% up to about 100 wt%, of the dispersion. 15 The dispersion may consists essentially of the particles, the dispersant, and the liquid, or the dispersion may comprise other ingredients that are commonly used in dispersions used in the inks, coatings, and/or adhesives, such as, for example, other dispersants; surfactants, such as, for example, nonionic and anionic surfactants; defoamers; and wetting agents. 20 [0025] In one aspect of the invention, the dispersant further comprises the sodium salt (R = Na*), 2,3-dihydroxynaphthalene-6-sulfonic acid sodium salt. The sodium salt is commercially available from Nantog Baisheng Chemicals Co. under the trade name "Dihydroxy R Salt" or "DHR". [0026] Surfactants may be present at levels of about 0.1 to about 10.0 wt% of the 25 dispersion. Nonionic surfactants are well know to those skilled in the art and can comprise at least one ethoxylates of alkyl phenols containing from about 8 to about 18 carbon atoms in a straight-or branched chain alkyl group, such as t-octyl phenol and t nonyl phenol with about 5 to about 30 moles of ethylene oxide; and ethoxylates of primary alcohols containing about 8 to about 18 carbon atoms in a straight or branched 30 chain configuration with about 5 to about 30 moles of ethylene oxide, for example, lauryl or myristyl alcohol condensed with about 16 moles of ethylene oxide. Anionic surfactants are well known to those skilled in the art. Anionic surfactants are salts, especially water soluble salts in which the cation comprise at least one of sodium, potassium, ammonium, or -9- WO 2007/082155 PCT/US2006/060151 substituted ammonium, such as the cations of ethanol amine, diethanol amine, and triethanol amine salts and in which the surfactant portion is negatively charged. These surfactants can comprise at least one C 8
-C
22 alkyl sulfates, alkyl sulfonates, alkyl sulfosuccinates, and alkylbenzene sulfonates, such as linear alkylbenzene sulfates and 5 sulfonates; sulfates of ethoxylated C8-C22 alkyl alcohols in which the alkyl group contains about 10 to about 22 and the polyoxyethylene chain contains about 0.5 to about 22 moles of ethylene oxide alkyl alcohol; and phosphates of alkyl alcohols, ethoxylated alkyl alcohols, and ethoxylated alkyl phenols. [0027] Defoamers may be present at levels of about 0.01 to about 3.0 wt % of the 10 dispersion. Defoamers can comprise at least one of silicones such as polyether modified dimethylsiloxanes, for example BYK 307 and BYK 333 (Byk Chemie, Wallingford, CT, USA), and acetylinic diols such as those sold under the SURFYNOL@ trademark (Air Products and Chemicals, Allentown, PA, USA). Wetting agents may be present at levels of about 0.1 to about 10.0 wt%. Wetting agents can comprise at least one of sodium 15 dioctylsulfosuccinate and acetylinic diols such as those sold under the DYNOL@ trademark (Air Products and Chemicals, Allentown, PA, USA). [0028] The particles can form a stable dispersion in the liquid. That is, the resulting dispersion does not exhibit separation of components, a dramatic increase in viscosity, and/or flocculation of the particles within 24 hours. Typically, the dispersion is stable for 20 at least seven days. This allows master batches to be prepared and stored until needed. [0029] In another aspect, the invention comprises a method for preparing the stable dispersion. The method comprises dispersing the particles in the liquid containing the dispersant. The dispersant is dissolved in the polar liquid and the pH adjusted, if necessary. For example, if the dispersion is ultimately to be used in a formulation that is 25 typically in the range of pH about 8 to about 9, such as many inks or coatings, the dispersant solution can be adjusted to this pH range by addition of about 10% aqueous sodium hydroxide or an amine such as AMP-95 (2-amino-2-methyl-1 -propanol). Then the particles are dispersed in the liquid containing the dispersant. The particles may be dispersed using equipment typically used in the ink, coating, and/or adhesive industries. 30 This equipment is well known to those skilled in the art, and includes, for example, ball mills, stirred bead mills, homogenizers, roll mills, and ultrasonication baths. [0030] The metal oxide particle dispersions may be supplied as a "solution" (i.e., low solids dispersion) or a very high solids (>70%) paste. Typically a relatively high solids -10- WO 2007/082155 PCT/US2006/060151 paste is useful in applications where the total liquid content of the final coating, such as in ink or adhesive applications, must be minimized. INDUSTRIAL APPLICABILITY 5 [0031] The dispersions of the invention contain relatively high levels of particles. The disperions may be used as master batches in the preparation of, for example, inks, coatings, and adhesives with enhanced mechanical, chemical, electrical, optical or magnetic properties. Because the dispersion is stable, it does not have to be prepared immediately before use. Large amounts can be prepared, which can be stored for future 10 use. [0032] The advantageous properties of this invention can be observed by reference to the following examples, which illustrate certain aspects of the invention and do not limit the scope of the invention or any claims appended hereto. 15 EXAMPLES Trade Name Chemical Description Alumina A spherical gamma alumina, BET particle size 15nm Alumina B spherical gamma alumina, BET particle size 30nm Alumina C spherical 70:30 gamma/delta alumina, BET particle size 47nm 20 Alumina D spherical gamma alumina, BET particle size 20nm Alumina E spherical gamma alumina, BET particle size 40nm Alumina F spherical gamma alumina, BET particle size 15nm Alumina G spherical alumina, BET particle size < 100nm Zirconia A spherical, BET particle size 15 nm 25 Zirconia B spherical, BET particle size < 100nm Titania A spherical anatase, BET particle size 17 nm AMP-95 2-Amino-2-methyl-1 -propanol DHR Salt 2,3-Dihydroxy-6-naphthalene sulfonic acid sodium salt Tiron Disodium salt monohydrate of 4-5-dihydroxy-1,3 benzenedisulfonic acid 30 - 11 - WO 2007/082155 PCT/US2006/060151 SO 3 Na OH HO SO 3 Na NaO 3 S OH HO M Tego Dispers 752W maleic acid/vinyl polyether copolymer, pH = 6 Disperbyk-190 non-ionic copolymer with carboxy anchor groups, pH = 7 5 Zetasperse 1400 acrylate graft copolymer [0033] Examples 1 - 10 in Table 1 were prepared by dissolving Tiron in the liquid, adding nanoalumina, and sonicating in an ultrasonication bath (Branson Model 3510) at 65C for the time shown. Physical properties are based upon visual inspection 10 immediately after sonication. Viscosity Measurement [0034] The sample were tested using a Brookfiled Model DVII+ at 20rpm with a #2 spindle. By "fluid" it is meant that the composition or dispersion has a viscosity of less 15 than about 500cp. By "paste" it is meant the composition is too thick to be poured out of its container. Particle Size and Zeta Potential [0035] Samples were diluted to 0.1 % solids in the same liquid used to make the 20 dispersion. Particle size and zeta potential were determined using a Malvern Nanosizer (Malvern, Worcestershire, UK) and Malvern Zetasizer@ (Malvern, Worcestershire, UK). [0036] Examples 1 and 2 demonstrated that, although nanoalumina can be dispersed in ethylene glycol (EG) at 30% solids, nanoalumina is difficult to disperse at 60% solids. [0037] Examples 3-7 demonstrated that the addition of Tiron yields fluid dispersion up 25 to 60% solids. [0038] Examples 8 and 9 demonstrated that alumina can be dispersed in glycerin at 30% solids with or without Tiron. It was an unexpected result that alumina was dispersed in EG with Tiron at 50% solids (example 6) and that little to no alumina was dispersed in water with Tiron at 50% solids (example 10). - 12- WO 2007/082155 PCT/US2006/060151 Table 1 Example Water Tiron Ethylene Glycerin Alumina Sonicated Physical glycol OF 650C, hrs properties 1 70 30 1 fluid 2 40 60 3 paste 3 2 68 30 1 fluid 4 2 58 40 1 fluid 5 2 58 40 3 fluid 6 2 48 50 1 fluid 7 2 40 60 3 fluid 8 2 68 30 2 fluid 9 68 30 2 fluid 10 48 2 50 1 paste Composition is dry wt % [0039] The Examples listed in Table 2 were prepared in the same manner as those in 5 Table 1 except that the samples were sonicated 2 hrs at 65C. Examples 11-30 in Table 2 demonstrate the dispersion of several different alumina samples in different liquids and mixtures of liquids that used either Tiron or DHR salt. Dispersion viscosity, particle size and zeta potential were used to gauge dispersion quality. The commercially available nanopowders typically are comprised of aggregates containing hundreds of 10 thousands of primary nanoparticles. These aggregates are several microns in diameter. The ability to disperse these aggregates into much smaller clusters is a gauge of dispersion efficacy. Similarly, zeta potential can also be used as a measure of dispersion stability. The zeta potential measures the charge on the particle surface. A relatively high negative or positive zeta potential means that the particles will repel each 15 other rather than being attracted and flocculating. Because inks, coatings and adhesives are comprised of anionic ingredients, an anionic nanodispersion is normally effective. [0040] A comparison of Examples 11 and 12 illustrates unexpected results. While surface charge is common for particles dispersed in aqueous media, it is not typically observed in non-aqueous media. Furthermore, the addition of Tiron shifted the charge 20 from a relatively high positive value to an even higher negative value. As described above, an anionic surface charge is typically more suitable for formulating purposes. Example 13 demonstrated that it is difficult to disperse alumina in EG at high solids. Examples 14-19 demonstrated that Tiron was used to disperse different nanoaluminas in EG at up to 60% solids. These dispersions had a relatively low viscosity and a highly 25 negative zeta potential. In Examples 18 and 19, AMP-95 an amine which is typically used in many coating and adhesive formulations, was included in the dispersion without -13- WO 2007/082155 PCT/US2006/060151 negative impact. Similarly, Examples 20-22 demonstrated that DHR salt can be used to disperse nanoalumina in EG at high solids to achieve a low viscosity, small particle size dispersion with a highly negative zeta potential. [0041] Examples 23-29 demonstrated that Tiron and DHR salt were used to form low 5 viscosity dispersions of nanoalumina at high solids content in polar liquids or mixtures of polar liquids. Table 2 Dispersion of alumina in polar liquids with Tiron and DHR salt Ex. Alumina DHR Tiron AMP- Ethyl- Glyc Propyl Water Vis- Par- Zeta (type) salt 95 ene erin ene cosity ticle poten glycol glycol 20rpm size, tial cps nm mv 11 30 (A) 70 fluid 124 +55 12 30(A) 2 68 fluid 126 -79 13 60(A) 40 paste 141 14 58.3(A) 2.9 38.8 fluid 111 15 40(A) 2 58 fluid 116 16 30 C 2 68 fluid 129 17 58.8 (C) 2 39.4 fluid 120 18 57.4(C) 2.9 1.4 38.3 500 19 58.3 (A) 1.9 1 38.8 1150 130 -84 20 29.4 (A) 1.4 0.7 68.6 Fluid 118 -87 21 30 (A) 2 1 67 Fluid 113 -76 22 58.3 (A) 1.9 1 37.8 Fluid 114 -82 23 57.7 (B) 1.9 1.9 9.6 28.8 33 24 50(B) 2 1 50 530 25 49(B) 2 49 140 26 48.5 (B) 1.9 1 24.3 24.3 535 27 48.5 (B) 1.9 1 24.3 24.3 1325 28 48.5 (B) 1.9 1 24.3 24.3 108 29 48.5(B) 1.9 1 24.3 24.3 530 Compositions are in wt % 10 [0042] The Examples in Table 3 were prepared in the same manner as those in Table 2. Table 3 compares Tiron and DHR salt with two structurely similar molecules, 3,4 dihyrdoxybenzoic acid, sodium salt and 4,5-dihydroxynaphthalene-2,7-disulfonic acid, sodium salt. These experiments were performed with 50% nanoalumina, 2% dispersant and 1% AMP-95. The dispersions that were made with Tiron and DHR salt 15 (Ex. 30-33) were relatively low viscosity, small particle size and colorless upon aging at room temperature for one week. The 3,4 dihyrdoxybenzoic acid, sodium salt did not form a dispersion (Ex. 34). The 4,5-dihydroxynaphthalene-2,7-disulfonic acid, sodium salt did form a relatively low viscosity dispersion (Ex. 35) with a small particle size but produced a dark pink color upon aging. The presence of color is normally unacceptable -14- WO 2007/082155 PCT/US2006/060151 in most applications where nanoparticles would be used, such as inks, coatings, and adhesives. Table 3 Comparison with structurally similar molecules 50% Alumina, 2% dispersant, 1% AMP-95 Example Dispersant Alumina 20 rpm 1 week visual Particle viscosity observation size, nm 30 Tiron B 157 Fluid, white 126 31 Tiron E 160 Fluid, white 141 32 Tiron D 178 Fluid, white 107 33 DHR salt B 189 Fluid, white 133 34 3,4-dihydroxy B paste 197 benzoic acid, sodium salt 35 4,5-dihyrdroxy B 277 Fluid, dark 127 naphth.2,7- pink disulfonic acid, sodium salt 36 None B paste . 191 5 [0043] The Examples in Table 4 were prepared in the same manner as those in Table 2. The Examples in Table 4 demonstrate that Tiron was used effectively to disperse other nanometal oxides in EG. 10 Table 4 Dispersion of other metal oxides Example Titania Zirconia Alumina Zirconia Ethylene Tiron Viscosity A A G B glycol 37 20 78 2 Dispersed well, fluid 38 20 78 2 Dispersed well, fluid 39 20 78 2 Dispersed well, fluid 40 30 68 2 Dispersed well, fluid [0044] The Examples in Table 5 were prepared in the same manner as those in Table 2. Examples in Table 5 demonstrate that Tiron was also effective in dispersing 15 alumina in propylene glycol to yield dispersions with relatively low viscosity, small particle size and a highly negative zeta potential. - 15- WO 2007/082155 PCT/US2006/060151 Table 5 Dispersions in propylene glycol Example Propylene Tiron AMP- Alumina Particle Zeta Viscosity, glycol 95 (type) size, potential, 20 rpm, nm mv cps 41 48.5 2 1 48.5 (A) 123 -46 500 42 48.5 2 1 48.5 (B) 134 -47 305 Compositions are in wt % Example 43: Preparation of dispersion on three roll mill 5 [0045] The following composition was dispersed and milled using a three roll mill (Exakt, Model 80E): Tiron 4g Ethylene glycol 82g AMP-95 2g 10 Alumina B 121g [0046] The mixture was passed through the mill three times with a gap opening of 10 microns. The final dispersion was a paste containing 82% nano alumina. This paste was diluted to 40% solids with water. The viscosity of the aqueous dispersion was 92.5 cps. 15 The particle size was 129 nm and the zeta potential was -51.6 mv. If desired, the dispersion is substantially free of water during milling and then optionally diluted with water. [0047] Table 6 lists the dielectric constants of a number of different liquids. The dielectric constant is indicative of the polarity of a liquid with more polar liquids having 20 higher values. The dielectric constant is also indicative of the liquids ability to dissolve ionic compounds and maintain charged species in solution. The results in Examples 1-43 indicate that any liquid with a dielectric constant in the range of 35.0 - 68.1 would be useful in this invention. -16- WO 2007/082155 PCT/US2006/060151 Table 6 Dielectric Constants of Selected Liquids* Liquid Dielectric constant, 25C N-methylpyrrolidone 32.0 Methanol 32.6 propylene glycol 35.0 dimethylformamide 36.7 ethylene glycol 37.0 Acetonitrile 37.5 Furfural 41 Glycerin 42.5 1:1 water/ethylene glycol 57.8** 3:1 water/ethylene glycol 68.1** Water 78.5 * Data obtained from CRC Handbook of Chemistry and Physics ** Value weighted average value calculated from the dielectric constants of neat component 5 [0048] Examples 44-49 were prepared by placing the samples in a sonication bath for 2 hrs at 65C. Tego Dispers 752W and ZetaSperse 1400 are polymeric dispersants. The results of Examples 44-49 are set forth below in Table 7. [0049] Examples 44-49 show the effect of using different blend ratios of either 10 ZetaSperse 1400 or Tego Dispers 752W with Tiron. As the Tiron level increases from about 0 to about 0.5 to about 1.0 parts, the percentage of particles below about 1 00nm typically increases for both the ZetaSperse and Tego blends. Table 7 Dispersion of ITO Nanoparticles in water with Tiron and Commercial Dispersant Ex. ITO Water Tiron Tego Dispers 752W ZetaSperse Particle size, nm 1400 (% of particles) 44 40 58 2 98(22) 269 (78) 45 40 58 2 95 (32) ___1 219(68) 46 40 58 0.5 1.5 94(38) 213 (62) 47 40 58 0.5 1.5 88(64) 219 (36) 48 40 58 1 1 92(56) 226 (44) 49 40 58 1 1 90(63) 209 (37) 15 Compositions are in wt % -17- WO 2007/082155 PCT/US2006/060151 [0050] Examples 50-55 were prepared by placing the samples in a sonication bath for 2 hrs at 65C. Tego Dispers 752W and Disperbyk 190 are polymeric dispersants designed for use in aqueous media. [0051] Examples 52 and 53 show that both 0.5 and 1.0 parts of Disperbyk 190 are less 5 effective, than blends, in stabilizing a dispersion of nanoparticle ZnO in water. A combination of Disperbyk 190 with Tiron (Example 54) yields a stable dispersion with a particle size similar to that which can be achieved with Tiron alone (Examples 50 and 51). Similarly, a combination of Tego Dispers 752W with Tiron (Example 55) yields a stable dispersion with a particle size similar to that which can be achieved with Tiron 10 alone (Examples 50 and 51). Table 8 Dispersion of ZnO Nanoparticles in water with Tiron and Commercial Dispersant Ex. ZnO Water Tiron Tego Dispers 752W Disperbyk Particle 190 size, nm 50 10 58 0.5 113 51 10 58 1 100 52 10 58 0.5 Flocculated 53 10 58 1 Flocculated 54 10 58 0.5 __0.5 121 55 10 58 0.5 0.5 116 Compositions are in wt % 15 [0052] Examples 56-59 were prepared by placing the samples in a sonication bath for 2 hrs at 65C. As illustrated by Examples 56 and 57, Disperbyk 190 and Tego 752W alone did not produce ITO dispersions with greater than 50% of the particles being less than 100nm. By adding about 0.4% Tiron to a dispersion made with Disperbyk 190 the 20 particle size was reduced from about 340 nm to about 108 nm. Table 9 Dispersion of ITO in water with Tiron and Commercial Dispersant Ex. ITO Water Tiron Tego 752W Disperbyk Particle 190 size, nm (% of particles) 56 40 58 2 340 (100) 57 40 58 2 94.4 (32.2) 227 (67.8) 58 40 58 2 109(100) 59 40 57.6 0.4 12 108 (100) Compositions are in wt % - 18 -
Claims (12)
1. A composition comprising: a) about 0.1 wt% to about 25 wt%, based on the total weight of the dispersion, of a dispersant comprising at least one ortho-dihydroxy aromatic 5 sulfonic acid salt,, b) about 1 wt% to about 90 wt%, based on the total weight of the dispersion, comprising particles selected from the group consisting of metal oxide particles, particles having a metal oxide surface, and mixtures thereof, in which the particles have a particle size of about 1 nm to about 2000 nm; and 10 c) about 10 wt% to about 90 wt%, based on the total weight of the dispersion, of at least one liquid selected from the group consisting of ethylene glycol, propylene glycol, glycerin, glycol mono-ethers of the formula R"OCH 2 CH 2 OH, in which R" is an alkyl group of one to four carbon atoms, and mixtures thereof; in which the particles are dispersed in the liquid. 15
2. The composition of Claim 1 in which the dispersant comprises disodium salt monohydrate of 4-5-dihydroxy-1,3 benzenedisulfonic acid.
3. The composition of Claim 1 in which the polar liquid comprises at least one 20 member selected from the group consisting of ethylene glycol, propylene glycol, glycerin, and mixtures thereof.
4. The composition of Claim 1 in which the particles have a particle size of about 1 nm to about 100 nm. 25
5. The composition of Claim 1 in which the particles comprise at least one member selected from the group consisting of alumina particles, indium tin oxide particles, zirconia particles, titania particles, iron oxide particles, ceria particles, zinc oxide, aluminum metal particles with a surface layer of aluminum oxide, and mixtures thereof 30
6. The composition of Claim 3 in which the liquid comprises ethylene glycol and water. -19- WO 2007/082155 PCT/US2006/060151
7. The composition of Claim 1 in which the dispersant further comprises 2,3 dihydroxy-6-naphthalene sulfonic acid sodium salt.
8. The composition of Claim 1 in which the particles comprise alumina particles. 5
9. The composition of Claim 1 wherein the liquid comprises propylene glycol.
10. The composition of Claim 1 wherein the liquid further comprises at least one amine compound. 10
11. The composition of Claim 1 wherein the liquid has a dielectric constant of about
35.0 to at least about 68.1. 12. The composition of Claim 1 wherein the particles have a negative Zeta potential. 15 13. The composition of Claim 1 wherein the composition has a viscosity of less than about 1000cp. 14. The composition of Claim 1 wherein particles comprise at least one member 20 selected from the group consisting of metal oxides, silica, silane coated metal oxides, and metal particles. 15. A composition comprising: a) about 10 wt.% to about 90wt.% water, 25 b) about 0.1 wt% to about 25 wt%, based on the total weight of the dispersion, of at least one dispersant comprising at least one orthodihydroxyaromatic sulfonic acid salt, c) about 1 wt% to about 90 wt%, based on the total weight of the dispersion, of particles comprising at least one member selected from the group 30 consisting of metal oxide particles, particles having a metal oxide surface, and mixtures thereof, in which the particles have a particle size of about 1 nm to about 2000 nm; d) optionally about 10 wt% to about 90 wt%, based on the total weight of the dispersion, comprising at least one member selected from the group - 20 - WO 2007/082155 PCT/US2006/060151 consisting of water, ethylene glycol, propylene glycol, glycerin, glycol mono ethers of the formula R"OCH 2 CH 2 OH, in which R" is an alkyl group of one to four carbon atoms, and mixtures thereof, e) optionally about 1 wt% to about 99 wt%, based upon the total weight of 5 the dispersion, comprising at least one member selected from the group consisting of water-borne polymers such as emulsion polymers, aqueous polymer dispersions, aqueous polymer colloids, and aqueous polymer solutions. These water-borne polymers may comprise at least one of urethane, acrylic, styrene acrylic, siloxane, vinyl acetate, vinyl chloride and among other polymers; and; 10 f) optionally all or part of the metal oxide nanoparticles can be replaced with about 10 wt% to about 90 wt%, based on the total weight of the dispersion, comprising at least one member selected from the group of metal nanoparticles 16. The composition of Claim 15 wherein the dispersant further comprises at 15 least one member selected from the group consisting of polyoxyethylenated long-cain amines, polyoxyethylenated alkyphenols, polyoxyethylenated alcohols, polyoxyethylenated carboxylic acids, polyoxyethylenated sorbitol esters, polyoxyethylenated alkanolamides, long-chain carboxylic acid esters, poly(ethylene oxide-co-propylene oxide), and sulfonated, sulfated, phosphated or phosphonated 20 derivatives of the foregoing; polyacrylates, polyesters, polyamides, maleic acid/vinyl polyether copolymer, styrene-maleic acid copolymers, polyurethanes, polyimides, polyethers, polysilicones and amine, alcohol, acid and ester functionalized derivatives of the foregoing. 25 17. The composition of Claim 15 in which the particles comprise at least one member selected from the group consisting of alumina particles, indium tin oxide particles, zirconia particles, titania particles, iron oxide particles, ceria particles, zinc oxide aluminum metal particles with a surface layer of aluminum oxide, and mixtures thereof. 30 18. The composition of Claim 15 wherein at least about 50% of the particles are less than about 100nm. - 21 - WO 2007/082155 PCT/US2006/060151 19. The composition of Claim 15 wherein the particles comprise at least one member selected from the group consisting of alumina particles, indium tin oxide particles and zinc oxide particles. 5 20. The composition of Claim 15 wherein the amount of dispersant is sufficient to impart electrostatic and steric stabilization. 21. The composition of Claim 15 wherein the dispersant comprises a compound having the formula: SO 3 Na OH 10 NaO 3 S OH\ 22. The composition of Claim 15 wherein the dispersant comprises a compound having the formula: HO SO 3 Na 15 HO 23. The composition of Claim 15 wherein the dispersant comprises at least one compound selected from the group of compounds having a formula: S0 3 X R1 R2 S3 R1 OH HO SO3XR1O HO R5 NaO 3 S OH 20 R3 R4 R2 -22- WO 2007/082155 PCT/US2006/060151 wherein R1-R4 comprise H and/or alkyl, and X comprises at least one member selected from the group consting of Na, K, Li, NH4, R1NH2, R2NH, and R3N. 5 10 - 23 -
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US73073505P | 2005-10-27 | 2005-10-27 | |
US60/730,735 | 2005-10-27 | ||
US79725106P | 2006-05-02 | 2006-05-02 | |
US60/797,251 | 2006-05-02 | ||
US11/583,439 US20100096601A1 (en) | 2005-10-27 | 2006-10-19 | Molecules with complexing groups for aqueous nanoparticle dispersions and uses thereof |
US11/583,439 | 2006-10-19 | ||
PCT/US2006/060151 WO2007082155A2 (en) | 2005-10-27 | 2006-10-23 | Molecules with complexing groups for aqueous nanoparticle dispersions and uses thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
AU2006347616A1 true AU2006347616A1 (en) | 2007-07-19 |
Family
ID=38472897
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2006347616A Abandoned AU2006347616A1 (en) | 2005-10-27 | 2006-10-23 | Molecules with complexing groups for aqueous nanoparticle dispersions and uses thereof |
Country Status (5)
Country | Link |
---|---|
US (1) | US20100096601A1 (en) |
EP (1) | EP1951417A2 (en) |
KR (1) | KR20080077613A (en) |
AU (1) | AU2006347616A1 (en) |
WO (1) | WO2007082155A2 (en) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070078190A1 (en) * | 2005-09-30 | 2007-04-05 | Distefano Frank V | Use of 2,3-dihydroxynaphthalene-6-sulfonic acid salts as dispersants |
WO2008024702A2 (en) * | 2006-08-21 | 2008-02-28 | Air Products And Chemicals, Inc. | Zinc oxide nanoparticle dispersions |
US8512467B2 (en) | 2006-08-21 | 2013-08-20 | Air Products And Chemicals, Inc. | Zinc oxide nanoparticle dispersions |
US9006325B2 (en) * | 2006-10-12 | 2015-04-14 | Suncolor Corporation | Polymeric composition |
KR100791555B1 (en) * | 2007-02-02 | 2008-01-03 | 주식회사 선진화학 | A disperse system having fine powder-typed inorganic metal oxide dispersed in water and preparing method for the same |
US8791191B2 (en) | 2009-02-03 | 2014-07-29 | Buehler Partec Gmbh | Zinc oxide particles which have been modified with phosphonocarboxylic acid and use of zinc oxide particles |
EP2241602A1 (en) | 2009-04-17 | 2010-10-20 | Bühler PARTEC GmbH | Zinc oxide particle modified with phosphonocarboxylic acid and use of same |
DE102009059276A1 (en) * | 2009-12-22 | 2011-06-30 | Rent-a-Scientist GmbH, 93059 | Formulation with metal nanoparticles |
EP2607408A1 (en) * | 2011-12-21 | 2013-06-26 | Rhein Chemie Rheinau GmbH | Method for dust-free manufacture of master batches containing nano-particles (CNT) in high viscosity rubbers by means of a three roll device |
EP2861526A4 (en) * | 2012-06-18 | 2015-12-16 | Innova Dynamics Inc | Agglomerate reduction in a nanowire suspension stored in a container |
CA2989598A1 (en) * | 2015-06-18 | 2016-12-22 | Dow Global Technologies Llc | Viscoelastic polyurethane foam with aqueous polymer dispersant |
WO2017069143A1 (en) * | 2015-10-20 | 2017-04-27 | 凸版印刷株式会社 | Coating solution and gas barrier laminate |
WO2017210439A1 (en) * | 2016-06-02 | 2017-12-07 | Dow Global Technologies Llc | Viscoelastic polyurethane foam with coating |
CN111630141B (en) * | 2018-01-23 | 2022-07-19 | 赢创运营有限公司 | Polymer-inorganic nanoparticle compositions, methods of manufacture thereof, and use thereof as lubricant additives |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0346139A2 (en) * | 1988-06-10 | 1989-12-13 | W.R. Grace & Co.-Conn. | Corrosion control |
DE19846096A1 (en) * | 1998-10-07 | 2000-04-13 | Bayer Ag | Preparation of suspensions of ternary oxides for printing inks |
EP1219687A1 (en) * | 2000-12-20 | 2002-07-03 | Basf Corporation | Dispersions for use in ink jet inks |
EP1529764A1 (en) * | 2003-11-10 | 2005-05-11 | Howmedica Osteonics Corp. | Method of producing a ceramic component |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2709655A (en) * | 1952-06-28 | 1955-05-31 | Gen Aniline & Film Corp | Diazotype photoprinting material |
US2746863A (en) * | 1954-02-10 | 1956-05-22 | Gen Aniline & Film Corp | Light sensitive diazotype material |
NL279582A (en) * | 1958-07-03 | |||
US3420666A (en) * | 1964-10-15 | 1969-01-07 | Gaf Corp | Two-component heat developing diazotypes |
US5223176A (en) * | 1988-09-30 | 1993-06-29 | Nissan Chemical Industries, Ltd. | Zirconia sol and method for making the same |
JP3827141B2 (en) * | 1998-01-27 | 2006-09-27 | ロード コーポレーション | Water-based primer or paint |
DE19907704A1 (en) * | 1999-02-23 | 2000-08-24 | Bayer Ag | Nano-scale precipitating zinc oxide used e.g. for protecting UV-sensitive organic polymers consists of particles having an average specified primary particle diameter |
US20050227075A1 (en) * | 2004-04-13 | 2005-10-13 | Eastman Kodak Company | Derivatized nanoparticle comprising metal-ion sequestrant |
US7357979B2 (en) * | 2004-04-13 | 2008-04-15 | Eastman Kodak Company | Composition of matter comprising polymer and derivatized nanoparticles |
US7361275B2 (en) * | 2004-04-13 | 2008-04-22 | Eastman Kodak Company | Use of derivatized nanoparticles to minimize growth of micro-organisms in hot filled drinks |
US7311933B2 (en) * | 2004-04-13 | 2007-12-25 | Eastman Kodak Company | Packaging material for inhibiting microbial growth |
US20070049659A1 (en) * | 2005-08-25 | 2007-03-01 | Quay Jeffrey R | Functionalized alumina particles for polymer composites |
US20070078190A1 (en) * | 2005-09-30 | 2007-04-05 | Distefano Frank V | Use of 2,3-dihydroxynaphthalene-6-sulfonic acid salts as dispersants |
-
2006
- 2006-10-19 US US11/583,439 patent/US20100096601A1/en not_active Abandoned
- 2006-10-23 KR KR1020087012722A patent/KR20080077613A/en not_active Application Discontinuation
- 2006-10-23 EP EP06851169A patent/EP1951417A2/en not_active Withdrawn
- 2006-10-23 WO PCT/US2006/060151 patent/WO2007082155A2/en active Application Filing
- 2006-10-23 AU AU2006347616A patent/AU2006347616A1/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0346139A2 (en) * | 1988-06-10 | 1989-12-13 | W.R. Grace & Co.-Conn. | Corrosion control |
DE19846096A1 (en) * | 1998-10-07 | 2000-04-13 | Bayer Ag | Preparation of suspensions of ternary oxides for printing inks |
EP1219687A1 (en) * | 2000-12-20 | 2002-07-03 | Basf Corporation | Dispersions for use in ink jet inks |
EP1529764A1 (en) * | 2003-11-10 | 2005-05-11 | Howmedica Osteonics Corp. | Method of producing a ceramic component |
Non-Patent Citations (1)
Title |
---|
SANTOS L R B ET AL (2004): "Tin oxide nanoparticle formation using a surface modifying agent", JOURNAL OF THE EUROPEAN CERAMIC SOCIETY, Vol. 24, no. 15-16, pages 3713-3721 * |
Also Published As
Publication number | Publication date |
---|---|
KR20080077613A (en) | 2008-08-25 |
US20100096601A1 (en) | 2010-04-22 |
EP1951417A2 (en) | 2008-08-06 |
WO2007082155A3 (en) | 2008-01-24 |
WO2007082155A2 (en) | 2007-07-19 |
WO2007082155A9 (en) | 2007-11-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU2006347616A1 (en) | Molecules with complexing groups for aqueous nanoparticle dispersions and uses thereof | |
AU2006222746B2 (en) | Use of 2,3-dihydroxynaphthalene-6-sulfonic acid salts as dispersants | |
TWI359169B (en) | Process for the production of coated, finely parti | |
Tan et al. | In situ formed Mg (OH) 2 nanoparticles as pH-switchable stabilizers for emulsions | |
US11649367B2 (en) | Aqueous pigment dispersions | |
JP5295621B2 (en) | Bactericidal filler composition | |
JP2009057627A (en) | Thick nanocolloidal gold liquid, fine gold particle, and their manufacturing methods | |
US8512467B2 (en) | Zinc oxide nanoparticle dispersions | |
EP1953197A1 (en) | Hydrophobic Metal and Metal Oxide Particles with Unique Optical Properties | |
KR102613596B1 (en) | Titanium dioxide aqueous dispersion and method for producing the same | |
ES2618916T3 (en) | Stable nanoparticulate suspension and production procedure | |
KR20220045007A (en) | Coloring and Filler Paste Using Inorganic Particles with Coated Surface as Spacers | |
JP2005035809A (en) | Aqueous fullerene dispersion | |
CN101296744A (en) | Molecules with complexing groups for aqueous nanoparticle dispersions and uses thereof | |
CN111868304A (en) | Dispersion comprising colloidal silica particles and zinc cyanurate particles | |
KR20080095801A (en) | Acid-based polymeric dispersants with 2-[2-(2-methoxyethoxy)ethoxy]acetic acid | |
US20100190866A1 (en) | Advanced antimicrobial carbon black dispersion | |
CN101240124A (en) | Hydrophobic metal and metal oxide particles with unique optical properties | |
Liang et al. | A rheological investigation of the self-assembly and adsorption behavior of a surfactant salt | |
WO2022133564A1 (en) | Method for producing a hybrid antimicrobial and antiviral agent from copper nanoparticles and active organic compounds, an antimicrobial and antiviral agent thus produced, and use of the antimicrobial and antiviral agent | |
WO2008024702A2 (en) | Zinc oxide nanoparticle dispersions |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
DA3 | Amendments made section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS: AMEND THE PRIORITY DETAILS FROM NOT GIVEN TO 11/583,439 19 OCT 2006US |
|
MK5 | Application lapsed section 142(2)(e) - patent request and compl. specification not accepted |